Intimate Details from Tupac’s Prison Letter to Madonna

TMZ has published portions of a previously unseen prison letter from Tupac to Madonna filled with candid revelations about their romance and breakup.
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Tupack Shakur and Madonna

Rapper Tupac Shakur and pop star Madonna were introduced by actress Rosie Perez at the Soul Train Music Awards in 1993 and began a romance a year later.

A recently uncovered letter from rapper Tupac Shakur to ‘Queen of Pop’ Madonna, which will be up for auction at Gotta Have Rock and Roll later this month, has revealed intimate details of their relationship and how race may have ended it. 

In 2015, Madonna admitted in an interview with radio host Howard Stern that she had a secret romance with Shakur. Now TMZ has published portions of the revealing handwritten letter Tupac wrote to Madonna in 1995, while he was serving out a sentence for sexual abuse charges. 

Addressed to “M,” Tupac wrote how he was “struggling to find all the answers” and offered several apologies for their breakup. “I must apologize to you because like you said I haven’t been the kind of friend I know I am capable of being,” he wrote.

He then explains how race was a factor in their split. “For you to be seen with a black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open and exciting,” he explained. “But for me at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was.”

Tupac also expressed his anger over an interview in which Madonna allegedly said: “I’m off to rehabilitate all the rappers & basketball players.”

“Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” he wrote. “It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things . . .Can you feel me?”

In the end, Tupac, who would be murdered a little over a year later in a drive-by shooting, wrote that he never meant to hurt Madonna and reached out asking for her friendship. 

“I offer my friendship once again, this time stronger and focused. If you are still interested I would like to further discuss this with you but some of it couldn’t wait. I felt compelled to tell you . . . just in case anything happened to me,” he wrote. “ . . .Please be careful Madonna. Everyone is not as honorable as they seem there are those whose hearts bleed with envy & evil. They would not hesitate to do you harm! Let my 6 bullets be proof of that!”

Gotta Have Rock will auction off the complete letter between July 19-28. 

READ ARTICLE:  "A Letter to Tupac Shakur, 20 Years Later" by journalist, author and activist Kevin Powell.